Condensed cyclic compound and organic light-emitting device including the same

ABSTRACT

A condensed cyclic compound and an organic light-emitting device, the condensed cyclic compound being represented by Formula 1:

CROSS-REFERENCE TO RELATED APPLICATION

Korean Patent Application No. 10-2014-0100696, filed on Aug. 5, 2014, inthe Korean Intellectual Property Office, and entitled: “Condensed CyclicCompound and Organic Light-Emitting Device Comprising the Same,” isincorporated by reference herein in its entirety.

BACKGROUND

1. Field

Embodiments relate to a condensed cyclic compound and an organiclight-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs), which are self-emitting devices,may have advantages such as wide viewing angles, excellent contrast,quick response, high brightness, excellent driving voltagecharacteristics, and can provide multicolored images.

An organic light-emitting device may have a structure in which a firstelectrode, a hole transport region, an emission layer, an electrontransport region, and a second electrode are sequentially disposed inthis order on a substrate. Holes injected from the first electrode maymove to the emission layer via the hole transport region, whileelectrons injected from the second electrode may move to the emissionlayer via the electron transport region. Carriers such as the holes andelectrons may recombine in the emission layer to generate excitons. Whenthe excitons drop from an excited state to a ground state, light may beemitted.

SUMMARY

Embodiments are directed to a condensed cyclic compound and an organiclight-emitting device including the same.

According to one or more embodiments, there is provided a condensedcyclic compound represented by Formula 1:

wherein, in Formula 1,

A₁ and A₂ are each independently a C₆-C₂₀ aromatic ring or a C₂-C₂₀heteroaromatic ring, wherein A₁ and A₂ are not benzene at the same time;

L₁ to L₆ are each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

a1 to a6 are each independently selected from 0, 1, 2, and 3;

R₁ to R₆ are each independently selected from a hydrogen, a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁)(Q₂), —B(Q₃)(Q₄), and —Si(Q₅)(Q₆)(Q₇);

b1 to b6 are each independently selected from 0, 1, 2, and 3;

c1 and c2 are each independently selected from 0, 1, 2, and 3;

wherein at least one substituent of the substituted C₃-C₁₀ cycloalkylenegroup, the substituted C₁-C₁₀ heterocycloalkylene group, the substitutedC₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocyclolalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group is selectedfrom

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂),—B(Q₁₃)(Q₁₄), and —Si(Q₁₅)(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —B(Q₂₃)(Q₂₄), and—Si(Q₂₅)(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —B(Q₃₃)(Q₃₄), and —Si(Q₃₅)(Q₃₆)(Q₃₇),

wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent aromatic condensed heteropolycyclic group.

According to one or more embodiments, an organic light-emitting deviceincludes: a first electrode; a second electrode disposed opposite to thefirst electrode; and an organic layer disposed between the firstelectrode and the second electrode and including an emission layer,wherein the organic layer includes at least one of the above-describedcondensed cyclic compounds of Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

Features will be apparent to those of skill in the art by describing indetail exemplary embodiments with reference to the attached drawings inwhich:

FIG. 1 illustrates a schematic view of a structure of an organiclight-emitting device according to an embodiment;

FIG. 2 illustrates UV absorption and photoluminescence (PL) spectra ofCompound 5 obtained in Synthesis Example 1, and low-temperature PLspectrum thereof; and

FIG. 3 illustrates a cyclic voltammetry curve of Compound 5 of SynthesisExample 1.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter withreference to the accompanying drawings; however, they may be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. Rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey exemplary implementations to those skilled in the art.

In the drawing figures, the dimensions of layers and regions may beexaggerated for clarity of illustration. Like reference numerals referto like elements throughout.

As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of,” when preceding a list of elements, modify the entire listof elements and do not modify the individual elements of the list.

According to an embodiment, there is provided a condensed cycliccompound represented by Formula 1:

In Formula 1,

At and A₂ may be each independently a C₆-C₂₀ aromatic ring or a C₁-C₂₀heteroaromatic ring. In an implementation, A₁ and A₂ may not both be abenzene at the same time.

In Formula 1, A₁ and A₂ may be condensed rings each sharing carbon withan adjacent 6-membered ring (e.g., the 6 membered ring that includessilicon).

For example, A₁ and A₂ may be the same or differ from each other. WhenA₁ and A₂ are the same, A₁ and A₂ may not both be benzene.

In an implementation, the C₆-C₂₀ aromatic ring may be a benzene, anaphthalene, or an anthracene; and the C₁-C₂₀ heteroaromatic ring may bea pyridine, a pyridazine, a pyrimidine, a pyrazine, a triazine, aquinoline, an isoquinoline, a phthalazine, a naphthyridine, aquinoxalaine, a quinazoline, a cinnoline, a benzothiophene, abenzofuran, a dibenzothiophene, or a dibenzofuran.

In an implementation, A₁ may be a benzene, a naphthalene, or ananthracene; and A₂ may be a naphthalene or an anthracene.

In an implementation, A₁ and A₂ may be each independently a pyridine, apyridazine, a pyrimidine, a pyrazine, a triazine, a quinoline, anisoquinoline, a phthalazine, a naphthyridine, a quinoxalaine, aquinazoline, a cinnoline, a benzothiophene, a benzofuran, adibenzothiophene, or a dibenzofuran.

In an implementation, A₁ may be a benzene, a naphthalene, an anthracene,a pyridine, a pyridazine, a pyrimidine, a pyrazine, a triazine, aquinoline, an isoquinoline, a phthalazine, a naphthyridine, aquinoxalaine, a quinazoline, or a cinnoline; and A₂ may be anaphthalene, an anthracene, a pyridine, a pyridazine, a pyrimidine, apyrazine, a triazine, a quinoline, an isoquinoline, a phthalazine, anaphthyridine, a quinoxalaine, a quinazoline, or a cinnoline. However,embodiments of the present disclosure are not limited thereto.

In Formula 1, L₁ to L₆ may be each independently selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group.

In an implementation, L₁ to L₆ in Formula 1 may be each independentlyselected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isooxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzooxazolylene group, anisobenzooxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolyene group, animidazopyridinylene group, and an imidazopyrimidinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isooxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzooxazolylene group, anisobenzooxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolyene group, animidazopyridinylene group, and an imidazopyrimidinylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, an aC₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzooxazolylgroup, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group.

In an implementation, L₁ to L₆ in Formula 1 may be each independently agroup represented by one of Formulae 3-1 to 3-32:

In Formulae 3-1 to 3-32,

Y₁ may be O, S, C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₇);

Z₁ to Z₇ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino groups, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

d1 may be an integer selected from 1 to 4;

d2 may be an integer selected from 1 to 3;

d3 may be an integer selected from 1 to 6;

d4 may be an integer selected from 1 to 8;

d5 may be 1 or 2;

d6 may be an integer selected from 1 to 5; and

* and *′ may be binding sites with adjacent atoms.

In an implementation, L₁ to L₆ in Formula 1 may be each independently agroup represented by one of Formulae 4-1 to 4-23.

In Formulae 4-1 and 4-23, * and *′ may be binding sites with adjacentatoms.

In Formula 1, a1, which indicates the number of L₁s, may be selectedfrom 0, 1, 2, and 3. In an implementation, a1 may be 0 or 1. When a1 is0, *-(L₁)_(a1)-*′ may be a single bond. When a1 is 2 or greater, two ormore L₁s may be the same or differ from each other. In Formula 1, a2,a3, a4, a5, and a6 may be understood based on the description of a1 andthe structure of Formula 1.

In an implementation, a1 to a6 in Formula 1 may be each independently 0or 1.

In Formula 1, R₁ to R₆ may be each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —B(Q₃)(Q₄), and —Si(Q₅)(Q₆)(Q₇),wherein Q₁ to Q₇ may be the same as defined herein.

In an implementation, R₁ to R₆ in Formula 1 may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₂₀alkylgroup, a substituted or unsubstituted C₁-C₂₀ alkoxy group, a substitutedor unsubstituted C₆-C₂₀ aryl group, a substituted or unsubstitutedC₁-C₂₀ heteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₅)(Q₆)(Q₇), wherein Q₅ to Q₇ may be the same as defined herein.

In an implementation, R₁ to R₆ in Formula 1 may be each independentlyselected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group;

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic groupor a salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group; and

—Si(Q₅)(Q₆)(Q₇), wherein Q₅ to Q₇ may be the same as defined herein.

In an implementation, R₁ to R₆ in Formula 1 may be each independentlyselected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzooxazolyl group, a triazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzooxazolyl group, a triazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group,a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzooxazolyl group, a triazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group.

In an implementation, R₁ to R₆ in Formula 1 may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group,and a group represented by one of Formulae 6-1 to 6-49.

In Formulae 6-1 to 6-49, * may be a binding site with an adjacent atom.

In Formula 1, b1, which indicates the number of R₁s, may be selectedfrom 0, 1, 2 and 3. In an implementation, b1 may be 1 or 2. When b1 is 2or greater, two or more R₁s may be the same or differ from each other.In Formula 1, b2, b3, b4, b5, and b6 may be understood based on thedescription of b1 and the structure of Formula 1.

In Formula 1, c1, which indicates the number of*-[(L₁)_(a1)-(R₁)_(b1)]s, may be selected from 0, 1, 2, and 3. In animplementation, c1 may be 0 or 1. When c1 is 0, A₁ may be anunsubstituted ring. When c1 is 2 or greater, two or more*-[(L₁)_(a1)-(R₁)_(b1)] may be the same or differ from each other. InFormula 1, c2 may be understood based on the description of c1 and thestructure of Formula 1.

In an implementation, in Formula 1, c1 and c2 may be 0, a3 to a6 may be0, and b3 to b6 may be 1.

In an implementation, in Formula 1, when c1 and c2 are 0, a3 to a6 are0, and b3 to b6 are 1, R₃ to R₆ may be the same or differ from eachother.

In an implementation, the condensed cyclic compound represented byFormula 1 may be represented by one of Formulae 1A to 1E.

In Formulae 1A to 1E, L₁ to L₆, a1 to a6, R₁ to R₆, b1 to b6, c1, and c2may be the same as those defined above herein.

In an implementation, in Formulae 1A to 1E, L₁ to L₆ may be eachindependently a group represented by one of Formulae 4-1 to 4-23; and a1to a6 may be each independently 0 or 1.

In an implementation, in Formulae 1A to 1E, R₁ to R₆ may be eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, and a group represented by one of Formulae 6-1 to 6-49; and b1 tob6 may be 1.

In an implementation, the condensed cyclic compound of Formula 1 may berepresented by one of Formulae 1A(1) to 1A(5), Formulae 2A(1) to 2A(5),Formula 3A(1), and Formula 4A(1).

In Formulae 1A(1) to 1A(5), Formulae 2A(1) to 2A(5), Formula 3A(1), andFormula 4A(1), R₁, R₂, b1, and b2 may be the same as those definedherein, R_(3a) to R_(3g) may be each independently selected from thesame groups as those defined for R₃ herein, R_(4a) to R_(4g) may be eachindependently selected from the same groups as those defined for R₄herein, R_(5a) to R_(5g) may be each independently selected from thesame groups as those defined for R₅ herein, and R_(6a) to R_(6g) may beeach independently selected from the same groups as those defined for R₆herein.

In an implementation, the condensed cyclic compound represented byFormula 1 may be one of Compounds 1 to 7.

The condensed cyclic compound represented by Formula 1 may include acore represented by Formula 1′, and thus may have a high triplet energylevel (T1) and may be suitable as a material for organic light-emittingdevices, e.g., as a phosphorescent host.

In Formula 1, A₁ and A₂ may not be benzene at the same time. Forexample, if a condensed cyclic compound of Formula 1 were to includeboth A₁ and A₂ as benzene at the same time, the compound (e.g., CompoundA of Comparative Example 1, below) may have a relatively high glasstransition temperature (Tg), a relatively high triplet energy level(T1), and poor energy transfer characteristics, and thus may not besuitable for use as a material for organic light-emitting devices, e.g.,as a phosphorescent host.

The condensed cyclic compound of Formula 1 may be synthesized using asuitable organic synthesis method. Methods of synthesizing the condensedcyclic compound of Formula 1 may be understood, e.g., based on theexamples that will be described below.

The condensed cyclic compound of Formula 1 may be used or includedbetween a pair of electrodes of an organic light-emitting device. In animplementation, the condensed cyclic compound of Formula 1 may beincluded in an electron transport region, e.g., in an electron transportlayer.

According to another embodiment, an organic light-emitting device mayinclude a first electrode, a second electrode opposite to the firstelectrode, and an organic layer between the first electrode and thesecond electrode, the organic layer including an emission layer. Theorganic layer may include at least one condensed cyclic compoundrepresented by Formula 1 described above.

As used herein, “(for example, the organic layer) including at least onecondensed cyclic compound means that “(the organic layer) including oneof the condensed cyclic compounds of Formula 1, or at least twodifferent condensed cyclic compounds of Formula 1.”

In an implementation, the organic layer may include only Compound 1 asthe condensed cyclic compound. In this regard, Compound 1 may be presentin the emission layer of the organic light-emitting device. In animplementation, the organic layer may include Compounds 1 and 2 as thecondensed cyclic compounds. In this regard, Compounds 1 and 2 may bepresent both in the same layer (for example, in the emission layer) ormay be present in different layers (for example, in the emission layerand the electron transport layer, respectively).

The organic layer may include, e.g., i) a hole transport region betweenthe first electrode (anode) and the emission layer and including atleast one of a hole injection layer, a hole transport layer, a bufferlayer, and an electron blocking layer; and ii) an electron transportregion between the emission layer and the second electrode (cathode) andincluding at least one of a hole blocking layer, an electron transportlayer, and an electron injection layer. The emission layer may includethe condensed cyclic compound of Formula 1.

As used herein, the term “organic layer” refers to a single layer and/ora plurality of layers disposed between the first and second electrodesof the organic light-emitting device. A material in the “organic layer”is not limited to an organic material.

FIG. 1 illustrates a schematic sectional view of an organiclight-emitting device 10 according to an embodiment. Referring to FIG.1, the organic light-emitting device 10 may include a first electrode110, an organic layer 150, and a second electrode 190.

Hereinafter, a structure of an organic light-emitting device accordingto an embodiment and a method of manufacturing the same will now bedescribed with reference to FIG. 1.

A substrate (not shown) may be disposed under the first electrode 110 oron the second electrode 190 in FIG. 1. The substrate may be a glass ortransparent plastic substrate with good mechanical strength, thermalstability, transparency, surface smoothness, ease of handling, and waterresistance.

For example, the first electrode 110 may be formed by depositing orsputtering a first electrode-forming material on the substrate. When thefirst electrode 110 is an anode, a material having a high work functionmay be used as the first electrode-forming material to facilitate holeinjection. The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. Transparentand conductive materials such as indium oxide (ITO), indium zinc oxide(IZO), tin oxide (SnO₂), and zinc oxide (ZnO) may be used to form thefirst electrode. When the first electrode 110 is a semi-transmissiveelectrode or a reflective electrode, at least one material selected frommagnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag) may be used as amaterial for forming the first electrode.

The first electrode 110 may have a single-layer structure or amulti-layer structure including a plurality of layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO.

The organic layer 150 may be disposed on the first electrode 110. Theorganic layer 150 may include an emission layer (EML).

The organic layer 150 may include a hole transport region between thefirst electrode and the EML, and an electron transport region betweenthe EML and the second electrode.

For example, the hole transport region may include at least one of ahole injection layer (HIL), a hole transport layer (HTL), a bufferlayer, and an electron blocking layer (EBL).

For example, the electron transport region may include at least one of ahole blocking layer (HBL), an electron transport layer (ETL), and anelectron injection layer (EIL).

The hole transport region may have a single-layered structure includinga single material, a single-layered structure including a plurality ofdifferent materials, or a multi-layered structure including a pluralityof layers including different materials.

In an implementation, the hole transport region may have asingle-layered structure including a plurality of different materials,or a multi-layered structure of HIL/HTL, HIL/HTL/buffer layer,HIL/buffer layer, HTL/buffer layer, or HIL/HTL/EBL, wherein these layersforming a multi-layered structure are sequentially disposed on the firstelectrode 110 in the order stated above.

When the hole transport region includes a HIL, the HIL may be formed onthe first electrode 110 by using any of a variety of methods, e.g., byusing vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, inkjet printing, laser printing, laser induced thermalimaging (LITI), or the like.

When the HIL is formed using vacuum deposition, the depositionconditions may vary depending on a compound that is used to form the HILand the structure of the HIL. For example, the deposition conditions mayinclude a deposition temperature of about 100° C. to about 500° C., adegree of vacuum of about 10⁻⁸ to about 10⁻³ torr, and a deposition rateof about 0.01 to about 100 Å/sec.

When the HIL is formed using spin coating, the coating conditions mayvary depending on a compound that is used to form the HIL and thestructure of the HIL. For example, the coating conditions may include acoating rate of about 2,000 rpm to about 5,000 rpm and a heat treatmenttemperature of about 80° C. to about 200° C.

When the hole transport region includes a HTL, the HTL may be formed onthe first electrode 110 or the HIL by using any of a variety of methods,e.g., by using vacuum deposition, spin coating, casting,Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing,laser induced thermal imaging (LITI), or the like. When the HTL isformed using vacuum deposition or spin coating, the conditions fordeposition and coating for forming the HTL may be similar to theabove-described deposition and coating conditions for forming the HIL,and accordingly will not be described in detail.

In an implementation, the hole transport region may include at least oneof m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB,α-NPB, TAPC, HMTPD, DNTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)(PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201 below, and a compound represented by Formula 202 below.

In Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may be each independently defined as described above inconjunction with L₁ to L₆ in Formula 1;

xa1 to xa4 may be each independently selected from 0, 1, 2, and 3;

xa5 may be selected from 1, 2, 3, 4, and 5;

R₂₀₁ to R₂₀₄ may be each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may be each independently selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group,

xa1 to xa4 may be each independently 0, 1, or 2;

xa5 may be 1, 2, or 3;

R₂₀₁ to R₂₀₄ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, an azulenyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group. However, embodiments of thepresent disclosure are not limited thereto.

The compound of Formula 201 may be represented by Formula 201A.

For example, the compound of Formula 201 may be represented by Formula201A-1:

The compound of Formula 202 may be represented by Formula 202A:

In Formulae 201A, 201A-1, and 202A,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ may be defined asdescribed in conjunction with Formula 201;

R₂₁₁ may be defined as described in conjunction with R₂₀₃ in Formula201;

R₂₁₃ to R₂₁₆ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group.

In an implementation, in Formulae 201A, 201A-1, and 202A,

L₂₀₁ to L₂₀₃ may be each independently selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group,

xa1 to xa3 may be each independently 0 or 1,

R₂₀₃, R₂₁₁, and R₂₁₂ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, aphenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

R₂₁₃ and R₂₁₄ may be each independently selected from:

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

R₂₁₅ and R₂₁₆ may be each independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, C₁-C₂₀ alkyl group and C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, and a triazinyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; and

xa5 may be 1 or 2.

In Formulae 201A and 201A-1, R₂₁₃ and R₂₁₄ may be linked to each otherto form a saturated or unsaturated ring.

In an implementation, the compound represented by Formula 201 and/or thecompound represented by Formula 202 may be compounds HT1 to HT20illustrated below.

A thickness of the hole transport region may be about 100 Å to about10,000 Å, e.g., about 100 Å to about 1,000 Å. When the hole transportregion includes a HIL and a HTL, a thickness of the HIL may be about 100Å to about 10,000 Å, e.g., about 100 Å to about 1,000 Å, and a thicknessof the HTL may be about 50 Å to about 2,000 Å, e.g., about 100 Å toabout 1,500 Å. When the thicknesses of the hole transport region, theHIL, and the HTL are within these ranges, satisfactory hole transportcharacteristics may be obtained without a substantial increase indriving voltage.

The hole transport region may further include a charge-generatingmaterial to help improve conductivity, in addition to the materials asdescribed above. The charge-generating material may be homogeneously orinhomogeneously dispersed in the hole transport region.

The charge-generating material may be, e.g., a p-dopant. The p-dopantmay include one of quinone derivatives, metal oxides, and cyanogroup-containing compounds. Non-limiting examples of the p-dopant mayinclude quinone derivatives such as tetracyanoquinonedimethane (TCNQ),2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), andthe like; metal oxides such as tungsten oxide, molybdenum oxide, and thelike; and Compound HT-D1 below.

The hole transport region may further include at least one of a bufferlayer and an EBL, in addition to the HIL and HTL described above. Thebuffer layer may help compensate for an optical resonance distance oflight according to a wavelength of the light emitted from the EML, andthus may help improve light-emission efficiency. A material in thebuffer layer may be a suitable material used in the hole transportregion. The EBL may help block injection of electrons from the electrontransport region.

For example, a material for forming the EBL may include mCP, below.

The EML may be formed on the first electrode 110 or the hole transportregion by using any of a variety of methods, e.g., by using vacuumdeposition, spin coating, casting, Langmuir-Blodgett (LB) deposition,inkjet printing, laser printing, laser induced thermal imaging (LITI),or the like. When the EML is formed using vacuum deposition or spincoating, the deposition and coating conditions for forming the EML maybe similar to the above-described deposition and coating conditions forforming the HIL, and accordingly may not be described in detail.

When the organic light-emitting device 10 is a full color organiclight-emitting device, the EML may be patterned into a red emissionlayer, a green emission layer, and a blue emission layer to correspondto individual subpixels, respectively. In an implementation, the EML mayhave a structure in which a red emission layer, a green emission layer,and a blue emission layer are stacked upon one another, or a structureincluding a mixture of a red light-emitting material, a greenlight-emitting material, and a blue light-emitting material, and thusmay emit white light.

The EML may include the condensed compound represented by Formula 1.

The EML may include a host and a dopant. The host may include thecondensed cyclic compound represented by Formula 1.

The host may further include at least one of TPBi, TBADN, ADN (alsoreferred to as “DNA”), CBP, CDBP, and TCP, in addition to the condensedcyclic compound of Formula 1.

The dopant may include at least one of a fluorescent dopant and aphosphorescent dopant.

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401.

In Formula 401,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm);

X₄₀₁ to X₄₀₄ may be each independently a nitrogen or a carbon;

rings A₄₀₁ and A₄₀₂ may be each independently selected from asubstituted or unsubstituted benzene, a substituted or unsubstitutednaphthalene, a substituted or unsubstituted fluorene, a substituted orunsubstituted spiro-fluorene, a substituted or unsubstituted indene, asubstituted or unsubstituted pyrrole, a substituted or unsubstitutedthiophene, a substituted or unsubstituted furan, a substituted orunsubstituted imidazole, a substituted or unsubstituted pyrazole, asubstituted or unsubstituted thiazole, a substituted or unsubstitutedisothiazole, a substituted or unsubstituted oxazole, a substituted orunsubstituted isoxazole, a substituted or unsubstituted pyridine, asubstituted or unsubstituted pyrazine, a substituted or unsubstitutedpyrimidine, a substituted or unsubstituted pyridazine, a substituted orunsubstituted quinoline, a substituted or unsubstituted isoquinoline, asubstituted or unsubstituted benzoquinoline, a substituted orunsubstituted quinoxaline, a substituted or unsubstituted quinazoline, asubstituted or unsubstituted carbazole, a substituted or unsubstitutedbenzoimidazole, a substituted or unsubstituted benzofuran, a substitutedor unsubstituted benzothiophene, a substituted or unsubstitutedisobenzothiophene, a substituted or unsubstituted benzoxazole, asubstituted or unsubstituted isobenzoxazole, a substituted orunsubstituted triazole, a substituted or unsubstituted oxadiazole, asubstituted or unsubstituted triazine, a substituted or unsubstituteddibenzofuran, and a substituted or unsubstituted dibenzothiophene;

at least one substituent of the substituted benzene, the substitutednaphthalene, the substituted fluorene, the substituted spiro-fluorene,the substituted indene, the substituted pyrrole, the substitutedthiophene, the substituted furan, the substituted imidazole, thesubstituted pyrazole, the substituted thiazole, the substitutedisothiazole, the substituted oxazole, the substituted isoxazole, thesubstituted pyridine, the substituted pyrazine, the substitutedpyrimidine, the substituted pyridazine, the substituted quinoline, thesubstituted isoquinoline, the substituted benzoquinoline, thesubstituted quinoxaline, the substituted quinazoline, the substitutedcarbazole, the substituted benzoimidazole, the substituted benzofuran,the substituted benzothiophene, the substituted isobenzothiophene, thesubstituted benzoxazole, the substituted isobenzoxazole, the substitutedtriazole, the substituted oxadiazole, the substituted triazine, thesubstituted dibenzofuran, and the substituted dibenzothiophene may beselected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxyl group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₄₀₁)(Q₄₀₂),—Si(Q₄₀₃)(Q₄₀₄)(Q₄₀₅), and —B(Q₄₀₆)(Q₄₀₇),

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group,

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₄₁₁)(Q₄₁₂),—Si(Q₄₁₃)(Q₄₁₄)(Q₄₁₅), and —B(Q₄₁₆)(Q₄₁₇), and

—N(Q₄₂₁)(Q₄₂₂), —Si(Q₄₂₃)(Q₄₂₄)(Q₄₂₅), and —B(Q₄₂₆)(Q₄₂₇);

L₄₀₁ may be an organic ligand;

xc1 may be 1, 2, or 3; and

xc2 may be 0, 1, 2, or 3,

wherein Q₄₀₁ to Q₄₀₇, Q₄₁₁ to Q₄₁₇ and Q₄₂₁ to Q₄₂₇ may be eachindependently selected from a hydrogen, a C₁-C₆₀ alkyl group, aC₂-C₆₀alkenyl group, a C₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group.

For example, in Formula 401, L₄₀₁ may be a monovalent, divalent, ortrivalent organic ligand. For example, L₄₀₁ in Formula 401 may beselected from a halogen ligand (for example, Cl or F), a diketone ligand(for example, acetylacetonate, 1,3-diphenyl-1,3-propanedionate,2,2,6,6-tetramethyl-3,5-heptanedionate, or hexafluoroacetonate), acarboxylic acid ligand (for example, picolinate,dimethyl-3-pyrazolecarboxylate, or benzoate), a carbon monoxide ligand,an isonitrile ligand, a cyano ligand, and a phosphorous ligand (forexample, phosphine or phosphite). However, embodiments of the presentdisclosure are not limited thereto.

When A₄₀₁ in Formula 401 has at least two substituent groups, the atleast two substituent groups of A₄₀₁ may be linked to each other to forma saturated or unsaturated ring.

When A₄₀₂ in Formula 401 has at least two substituent groups, the atleast two substituent groups of A₄₀₂ 2 may be linked to each other toform a saturated or unsaturated ring.

When xc1 in Formula 401 is 2 or greater, a plurality of ligands

in Formula 401 may be identical to or different from each other. Whenxc1 in Formula 1 is 2 or greater, A₄₀₁ and A₄₀₂ may be linked to A₄₀₁and A₄₀₂ of another adjacent ligand, respectively, directly or via alinking group (for example, a C₁-C₅ alkylene group, —N(R′)— (where R′ isa C₁-C₁₀ alkyl group or a C₆-C₂₀ aryl group), or C(═O)—).

In an implementation, the phosphorescent dopant may include at least oneof Compounds PD1 to PD74.

In an implementation, the phosphorescent dopant may include PtOEP below.

In an implementation, the phosphorescent dopant may include Flr6 below.

In an implementation, the fluorescent dopant may further include atleast one of DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

In an implementation, the fluorescent dopant may include a compoundrepresented by Formula 501.

In Formula 501,

Ar₅₀₁ may be selected from:

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene,

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃), wherein Q₅₀₁ to Q₅₀₃ may be each independentlyselected from a hydrogen, C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, aC₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group;

L₅₀₁ to L₅₀₃ may be the same as those for L₂₀₁ defined herein;

R₅₀₁ and R₅₀₂ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazoly group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothio group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, and adibenzofuranyl group, and a dibenzothiophenyl group;

xd1 to xd3 may be each independently selected from 0, 1, 2, and 3; and

xb4 may be selected from 1, 2, 3, and 4.

The dopant may be included in the EML in an amount of, e.g., about 0.01part by weight to about 15 parts by weight, based on 100 parts by weightof the host.

The thickness of the EML may be about 100 Å to about 1,000 Å, e.g.,about 200 Å to about 600 Å. When the thickness of the EML is withinthese ranges, the EML may have good light emitting ability without asubstantial increase in driving voltage.

Next, the electron transport region may be disposed on the EML.

The electron transport region may include, e.g., at least one of a HBL,an ETL, and an EIL.

In an implementation, the electron transport region may have a structureincluding an ETL/EIL, or a HBL/ETL/EIL, wherein the layers forming astructure of the electron transport region may be sequentially stackedon the EML in the order stated above.

In an implementation, the organic layer 150 of the organiclight-emitting device 10 may include the electron transport regionbetween the EML and the second electrode 190, and the condensed cycliccompound of Formula 1 may be in the electron transport region.

The electron transport region may include a HBL. When the EML includes aphosphorescent dopant, the HBL may help reduce and/or help preventdiffusion of triplet excitons or holes into the ETL from the EML.

When the electron transport region includes a HBL, the HBL may be formedon the EML by using any of a variety of methods, e.g., by using vacuumdeposition, spin coating, casting, Langmuir-Blodgett (LB) deposition,inkjet printing, laser printing, laser induced thermal imaging (LITI),or the like. When the HBL is formed using vacuum deposition or spincoating, the deposition and coating conditions for forming the HBL maybe similar to the above-described deposition and coating conditions forforming the HIL, and accordingly may not be described in detail.

In an implementation, the HBL may include at least one of BCP and Bphen.However, embodiments of the present disclosure are not limited thereto.

A thickness of the HBL may be about 20A to about 1,000A, e.g., about 30Ato about 300A. When the thickness of the HBL is within these ranges, theHBL may have improved hole blocking ability without a substantialincrease in driving voltage.

The electron transport region may include an ETL. The ETL may be formedon the EML or the HBL by using any of a variety of methods, e.g., byusing vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, inkjet printing, laser printing, laser induced thermalimaging (LITI), or the like. When the ETL is formed using vacuumdeposition or spin coating, the deposition and coating conditions forforming the ETL may be similar to the above-described deposition andcoating conditions for forming the HIL, and accordingly may not bedescribed in detail.

In an implementation, the organic layer 150 of the organiclight-emitting device may include an electron transport region betweenthe EML and the second electrode 190. The electron transport region mayinclude at least one of the ETL and the EIL.

In an implementation, the ETL may include at least one of BCP, Bphen,Alq₃, Balq, TAZ, NTAZ, TSPO1, and TmPyPb.

In an implementation, the ETL may include at least one selected from acompound represented by Formula 601 and a compound represented byFormula 602.Ar₆₀₁-[(L₆₀₁)_(xe1)-E₆₀₁]_(xe2)  <Formula 601>

In Formula 601, Ar₆₀₁ may be selected from:

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene; and

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃) (wherein Q₃₀₁ to Q₃₀₃ may be each independentlyselected from a hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group);

L₆₀₁ may be the same as defined for L₂₀₁ herein;

E₆₀₁ may be selected from:

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group; and

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coroneryl group, an ovarenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group;

xe1 may be selected from 0, 1, 2, and 3; and

xe2 may be selected from 1, 2, 3, and 4.

In Formula 602,

X₆₁₁ may be N or C-(L₆₁₁)_(xe611)-R₆₁₁, X₆₁₂ may be N orC-(L₆₁₂)_(xe612)-R₆₁₂, X₆₁₃ may be N or C-(L₆₁₃)_(xe613)-R₆₁₃, and atleast one of X₆₁₁ to X₆₁₃ may be N;

L₆₁₁ to L₆₁₆ may be the same as defined for L₂₀₁ herein;

R₆₁₁ to R₆₁₆ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group,a phenyl group, a naphthyl group, an azulenyl group, a fluorenyl group,a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; and

xe611 to xe616 may be each independently selected from 0, 1, 2, and 3.

The compound of Formula 601 and the compound of Formula 602 may be eachindependently selected from Compounds ET1 to ET15:

A thickness of the ETL may be about 100A to about 1,000 Å, e.g., about150 Å to about 500 Å. When the thickness of the ETL is within theseranges, the ETL may have satisfactory electron transporting abilitywithout a substantial increase in driving voltage.

In an implementation, the ETL may further include a metal-containingmaterial, in addition to the above-described materials.

The metal-containing material may include a lithium (Li) complex.Non-limiting examples of the Li complex may include compound ET-D1(lithium quinolate (LiQ)), or compound ET-D2.

The electron transport region may include an EIL that may facilitateinjection of electrons from the second electrode 190.

The EIL may be formed on the ETL by using any of a variety of methods,e.g., by using vacuum deposition, spin coating, casting,Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing,laser induced thermal imaging (LITI), or the like. When the EIL isformed using vacuum deposition or spin coating, the deposition andcoating conditions for forming the EIL may be similar to theabove-described deposition and coating conditions for forming the HIL,and accordingly may not be described in detail.

The EIL may include at least one selected from LiF, NaCl, CsF, Li₂O,BaO, and LiQ.

A thickness of the EIL may be about 1A to about 100 Å, e.g., about 3A toabout 90A. When the thickness of the EIL is within these ranges, the EILmay have satisfactory electron injection ability without a substantialincrease in driving voltage.

The second electrode 190 may be disposed on the organic layer 150, asdescribed above. The second electrode 190 may be a cathode as anelectron injecting electrode. A material for forming the secondelectrode 190 may be, e.g., a metal, an alloy, an electricallyconductive compound, which have a low-work function, or a mixturethereof. Non-limiting examples of materials for forming the secondelectrode 190 may include lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag). In an implementation, a material for formingthe second electrode 190 may be ITO or IZO. The second electrode 190 maybe a reflective electrode, a semi-transmissive electrode, or atransmissive electrode.

Although the organic light-emitting device of FIG. 1 is described above,embodiments are not limited thereto.

As used herein, a C₁-C₆₀ alkyl group refers to a monovalent linear orbranched aliphatic hydrocarbon group having 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ alkyl group are a methyl group, anethyl group, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.A C₁-C₆₀ alkylene group refers to a divalent group having the samestructure as the C₁-C₆₀ alkyl group.

As used herein, a C₁-C₆₀ alkoxy group refers to a monovalent grouprepresented by —OA₁₀₁ (where A₁₀₁ is a C₁-C₆₀ alkyl group as describedabove). Non-limiting examples of the C₁-C₆₀ alkoxy group are a methoxygroup, an ethoxy group, and an isopropyloxy group.

As used herein, a C₂-C₆₀ alkenyl group refers to a hydrocarbon groupincluding at least one carbon double bond in the middle or terminal ofthe C₂-C₆₀ alkyl group. Non-limiting examples of the C₂-C₆₀ alkenylgroup are an ethenyl group, a propenyl group, and a butenyl group. AC₂-C₆₀ alkylene group refers to a divalent group having the samestructure as the C₂-C₆₀ alkenyl group.

As used herein, a C₂-C₆₀ alkynyl group refers to a hydrocarbon groupincluding at least one carbon triple bond in the middle or terminal ofthe C₂-C₆₀ alkyl group. Non-limiting examples of the C₂-C₆₀ alkynylgroup are an ethynyl group and a propynyl group. A C₂-C₆₀ alkynylenegroup refers to a divalent group having the same structure as the C₂-C₆₀alkynyl group.

As used herein, a C₃-C₁₀ cycloalkyl group refers to a monovalent,monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms.Non-limiting examples of the C₃-C₁₀ cycloalkyl group are a cyclopropylgroup, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, anda cycloheptyl group. A C₃-C₁₀ cycloalkylene group refers to a divalentgroup having the same structure as the C₃-C₁₀ cycloalkyl group.

As used herein, a C₁-C₁₀ heterocycloalkyl group refers to a monovalentmonocyclic group having 1 to 10 carbon atoms in which at least onehetero atom selected from N, O, P, and S is included as a ring-formingatom. Non-limiting examples of the C₁-C₁₀ heterocycloalkyl group are atetrahydrofuranyl group and a tetrahydrothiophenyl group. A C₁-C₁₀heterocycloalkylene group refers to a divalent group having the samestructure as the C₁-C₁₀ heterocycloalkyl group.

As used herein, a C₃-C₁₀ cycloalkenyl group refers to a monovalentmonocyclic group having 3 to 10 carbon atoms that includes at least onedouble bond in the ring but does not have aromacity. Non-limitingexamples of the C₃-C₁₀ cycloalkenyl group are a cyclopentenyl group, acyclohexenyl group, and a cycloheptenyl group. A C₃-C₁₀ cycloalkenylenegroup refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

As used herein, a C₁-C₁₀ heterocycloalkenyl group refers to a monovalentmonocyclic group having 1 to 10 carbon atoms that includes at least onedouble bond in the ring and in which at least one hetero atom selectedfrom N, O, P, and S is included as a ring-forming atom. Non-limitingexamples of the C₁-C₁₀ heterocycloalkenyl group are a 2,3-hydrofuranylgroup and a 2,3-hydrothiophenyl group. A C₁-C₁₀ heterocycloalkenylenegroup refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkenyl group.

As used herein, a C₆-C₆₀ aryl group refers to a monovalent, aromaticcarbocyclic group having 6 to 60 carbon atoms, and a C₆-C₆₀ arylenegroup refers to a divalent, aromatic carbocyclic group having 6 to 60carbon atoms. Non-limiting examples of the C₆-C₆₀ aryl group are aphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenylgroup, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀ arylgroup and the C₆-C₆₀ arylene group include at least two rings, the ringsmay be fused to each other.

As used herein, a C₁-C₆₀ heteroaryl group refers to a monovalent,aromatic carbocyclic group having 1 to 60 carbon atoms in which at leastone hetero atom selected from N, O, P, and S is included as aring-forming atom, and 1 to 60 carbon atoms. A C₁-C₆₀ heteroarylenegroup refers to a divalent, aromatic carbocyclic group having 1 to 60carbon atoms in which at least one hetero atom selected from N, O, P,and S is included as a ring-forming atom. Non-limiting examples of theC₁-C₆₀ heteroaryl group are a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group. When the C₁-C₆₀ heteroaryl group andthe C₁-C₆₀ heteroarylene group include at least two rings, the rings maybe fused to each other.

As used herein, a C₆-C₆₀ aryloxy group indicates —OA₁₀₂ (where A₁₀₂ is aC₆-C₆₀ aryl group as described above), and a C₆-C₆₀ arylthio groupindicates —SA₁₀₃ (where A₁₀₃ is a C₆-C₆₀ aryl group as described above).

As used herein, a monovalent non-aromatic condensed polycyclic grouprefers to a monovalent group having at least two rings condensed to eachother, in which only carbon atoms (for example, 8 to 60 carbon atoms)are exclusively included as ring-forming atoms and the entire moleculerepresents non-aromacity. A non-limiting example of the monovalentnon-aromatic condensed polycyclic group is a fluorenyl group. A divalentnon-aromatic condensed polycyclic group refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedpolycyclic group.

As used herein, a monovalent non-aromatic condensed heteropolycyclicgroup refers to a monovalent group having at least two rings condensedto each other, in which carbon atoms (for example, 2 to 60 carbon atoms)and a hetero atom selected from N, O, P, and S are ring-forming atomsand the entire molecule represents non-aromacity. A non-limiting exampleof the monovalent non-aromatic condensed heteropolycyclic group is acarbazolyl group. A divalent non-aromatic condensed heteropolycyclicgroup refers to a divalent group having the same structure as themonovalent non-aromatic condensed heteropolycyclic group.

As used herein, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxyl group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂),—B(Q₁₃)(Q₁₄), and —Si(Q₁₅)(Q₁₆)(Q₁₇),

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group,

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—B(Q₂₃)(Q₂₄), and —Si(Q₂₅)(Q₂₆)(Q₂₇), and

—N(Q₃₁)(Q₃₂), —B(Q₃₃)(Q₃₄), and —Si(Q₃₅)(Q₃₆)(Q₃₇),

wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

For example, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovarenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₁₁)(Q₁₂),—B(Q₁₃)(Q₁₄), and —Si(Q₁₅)(Q₁₆)(Q₁₇),

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovarenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group,

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovarenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a pentalenyl group, an indenylgroup, a naphthyl group, an azulenyl group, a heptalenyl group, anindacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovarenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₂₁)(Q₂₂),—B(Q₂₃)(Q₂₄), and —Si(Q₂₅)(Q₂₆)(Q₂₇), and

—N(Q₃₁)(Q₃₂), —B(Q₃₃)(Q₃₄), and —Si(Q₃₅)(Q₃₆)(Q₃₇),

wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a pentalenyl group, an indenylgroup, a naphthyl group, an azulenyl group, a heptalenyl group, anindacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovarenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group.

The acronym “Ph” used herein refers to a phenyl group, the acronym “Me”used herein refers to a methyl group, the acronym “Et” used hereinrefers to an ethyl group, and the acronym “ter-Bu” or “Bu^(t)” usedherein refers to a tert-butyl group.

One or more embodiments, which include condensed cyclic compounds, andorganic light-emitting devices including the same, will now be describedin detail with reference to the following examples. In the followingsynthesis example(s), the expression that “‘B’ instead of ‘A’ was used”means that the amounts of ‘B’ and ‘A’ were the same in equivalentamounts.

The following Examples and Comparative Examples are provided in order tohighlight characteristics of one or more embodiments, but it will beunderstood that the Examples and Comparative Examples are not to beconstrued as limiting the scope of the embodiments, nor are theComparative Examples to be construed as being outside the scope of theembodiments. Further, it will be understood that the embodiments are notlimited to the particular details described in the Examples andComparative Examples.

EXAMPLES Synthesis Example 1: Synthesis of Compound 5 (TPDSiN)

Synthesis of Compound (A)

5 g (17.5 mmol) of 2,3-dibromonaphthalene and 150 mL of a mixed solventof anhydrous THF and Et₂O (1:1) were put into a 500-mL 3-necked flask,and then cooled down to about −110° C. in a cooling bath (EtOH,Et₂O/Liq-N₂ bath.), followed by slowly adding 7.2 mL (2.88 mmol) ofn-BuLi (2.5 M) thereto. The resulting reaction mixture was stirred undera nitrogen atmosphere for about 30 minutes, and then a dilute solutionof 2.2 g (8.75 mmol) of dichlorodiphenylsilane in 80 mL of a mixedsolvent of anhydrous THF and Et₂O (1:1) was slowly dropwise added to thereaction mixture, followed by stirring at the same temperature for about30 minutes. After slowly raising temperature to ambient temperature, thereaction mixture was stirred for 12 hours, followed by adding distilledwater to terminate the reaction, extracting with diethyl ether threetimes (100 mL each time), drying with anhydrous magnesium sulfate(MgSO₄), and removing the solvent with a rotary evaporator. The residuewas separated by column chromatography (n-hexane/dichloromethane, 15:1)to obtain 1.15 g of Compound (A) as a white solid (Yield: 22%).

¹H NMR (300 MHz, DMSO-d₆) δ 7.42-7.51 (m, 14H), 7.86-7.84 (m, 6H), 8.63(s, 2H).

Synthesis of Compound 5 (TPDSiN)

1.15 g (1.94 mmol) of Compound (A) and 50 mL of anhydrous THF were putinto a 100-mL 3-necked flask, and then cooled down to about −78° C. in acooling bath (EtOAc/Liq-N₂ bath.), followed by adding 1.6 mL (0.64 mmol)of n-BuLi (2.5 M) thereto. The resulting reaction mixture was stirredunder a nitrogen atmosphere for about 1 hour, and then a dilute solutionof 0.98 g (3.88 mmol) of dichlorodiphenylsilane in 20 mL of anhydrousTHF was slowly dropwise added to the reaction mixture, followed bystirring at the same temperature for about 30 minutes. After slowlyraising temperature to ambient temperature, the reaction mixture wasstirred for 24 hours, followed by adding 30 mL of distilled water toterminate the reaction, extracting with Et₂O three times (50 mL eachtime), drying with anhydrous magnesium sulfate (MgSO₄), and removing thesolvent with a rotary evaporator. The residue was separated by columnchromatography (n-hexane/ethyl acetate, 20:1) to obtain 0.61 g ofCompound 5 (TPDSiN) as a white solid (Yield: 51%).

¹H NMR (300 MHz, DMSO-d₆) δ 7.55-7.65 (m, 14H), 7.88-7.96 (m, 14H), 8.21(d, 4H); HRMS (FAB+) m/z 616.21.

Evaluation Example 1: Characteristics Evaluation of Compound 5

Evaluation of Spectroscopic Characteristics of Compound 5

UV absorption and photoluminescence (PL) spectra of Compound 5, andlow-temperature PL spectrum thereof were measured using the methodsdescribed in Table 1. The results are shown in FIG. 2.

TABLE 1 “UV_solution” Compound 5 was dissolved in CHCl₃ to a spectrumconcentration of 1 × 10⁻⁵ M, and then UV absorption spectrum thereofwere measured at ambient temperature using a Shimadzu UV-350Spectrometer. “PL_solution” A solution of Compound 5 in CHCl₃ to aconcentration spectrum of 1 × 10⁻⁵ M was subjected to PL spectrummeasurement at ambient temperature using an ISC PC1 Spectrofluorometerequipped with a Xenon lamp. “PL_low A solution of Compound 5 in CHCl₃ toa concentration temperature” of 1 × 10⁻⁵ M was subjected to PL spectrumspectrum measurement at a low temperature (77 K) using an ISC PC1Spectrofluorometer equipped with a Xenon lamp.

Referring to FIG. 2, Compound 5 exhibited suitable spectroscopiccharacteristics for use as a material for organic light-emittingdevices.

Evaluation of Electrochemical Characteristics of Compound 5

Electrochemical characteristics of Compound 5 were measured using cyclicvoltammetry (CV) (Electrolyte: 0.1 M Bu₄NClO₄/Solvent: CH₂Cl₂/Electrode:3-electrode system (working electrode: GC, reference electrode: Ag/AgCl,auxiliary electrode; Pt)). The results are shown in FIG. 3.

Referring to FIG. 3, Compound 5 exhibited suitable electricalelectrochemical characteristics for use as a material for organiclight-emitting devices.

Evaluation of HOMO and LUMO Energy Levels of Compound 5

A lowest unoccupied molecular orbital (LUMO) energy level of Compound 5was calculated using a reduction onset in FIG. 3. A highest occupiedmolecular orbital (HOMO) energy level of Compound 5 was calculated usingan optical band gap (E_(g)) based on the UV absorption edge in FIG. 2.The results are shown in Table 2. For comparison, data obtained from theUV absorption and PL spectra are also shown in Table 2. The HOMO andLUMO energy levels represent absolute values.

TABLE 2 UV PL E_(T) E_(g) HOMO LUMO (nm) (nm) (eV) (eV) (eV) (eV) 250,273, 364 3.01 3.52 5.81 2.29 327, 341

Referring to Table 2, Compound 5 was found to have a HOMO-LUMO energygap that is suitable for used as a material, e.g., a host material, fororganic light-emitting devices.

Example 1

A 15 Ω/cm² (1,000 Å) ITO glass substrate (available from Corning Co.,Ltd) was cut to a size of 50 mm×50 mm×0.7 mm and then sonicated inisopropyl alcohol and pure water each for 5 minutes, and then cleaned byirradiation of ultraviolet rays for 30 minutes and exposure to ozone.The resulting ITO glass substrate was mounted into a vacuum depositionapparatus.

After DNTPD was deposited on the ITO anode to form an HIL having athickness of about 600A, NPB was deposited on the HIL to form a HTLhaving a thickness of about 100A, mCP was deposited on the HTL to forman electron blocking layer (EBL) having a thickness of about 200A, andthen Compound 5 (host) and FIr6 (dopant) were co-deposited in a weightratio of 90:10 to form an EML having a thickness of about 400A on theEBL.

Next, TSPO1 was deposited on the EML to form a first ETL having athickness of about 300A, and then TmPyPb was deposited on the first ETLto form a second ETL having a thickness of about 250A. Then, LiF wasdeposited on the second ETL to form an EIL having a thickness of about10A, and Al was then deposited on the EIL to form a cathode having athickness of about 1000A, thereby manufacturing an organiclight-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 1, instead of Compound 5, was used asa host to form the EML.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound A, below, instead of Compound 5, wasused as a host to form the EML.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that CBP, below, instead of Compound 5, was used asa dopant to form the EML.

Evaluation Example 2

Driving voltages, current densities, luminances, efficiencies, andhalf-lifetimes of the organic light-emitting devices of Examples 1 and 2and Comparative Examples 1 and 2 were evaluated using a KethleySource-Measure Unit (SMU 236) and a PR650 (Spectroscan) SourceMeasurement Unit. (available from Photo Research, Inc.). The results areshown in Table 3.

TABLE 3 Driving Current Lumi- Effi- Host of voltage density nance ciencyCIE Example EML (V) (mA/cm²) (cd/m²) (cd/A) x Example 1 Com- 6.5 4.16500 12 0.18 pound 5 Example 2 Com- 7.0 4.54 500 11 0.17 pound 1Comparative Com- 7.8 7.14 500 7 0.18 Example 1 pound A Comparative CBP7.5 8.33 500 6 0.19 Example 2

Referring to Table 3, it may be seen that the organic light-emittingdevices of Examples 1 and 2 had lower driving voltages and improvedefficiency characteristics, as compared to the organic light-emittingdevices of Comparative Examples 1 and 2.

As described above, according to the one or more of the aboveembodiments, an organic light-emitting device including the condensedcyclic compounds of Formula 1 may have a low driving voltage, a highefficiency and a high luminance.

Example embodiments have been disclosed herein, and although specificterms are employed, they are used and are to be interpreted in a genericand descriptive sense only and not for purpose of limitation. In someinstances, as would be apparent to one of ordinary skill in the art asof the filing of the present application, features, characteristics,and/or elements described in connection with a particular embodiment maybe used singly or in combination with features, characteristics, and/orelements described in connection with other embodiments unless otherwisespecifically indicated. Accordingly, it will be understood by those ofskill in the art that various changes in form and details may be madewithout departing from the spirit and scope of the present invention asset forth in the following claims.

What is claimed is:
 1. A condensed cyclic compound represented by one ofFormulae 1A to 1C and 1E:

wherein, in Formula 1A to 1C and 1E, L₁ to L₆ are each independentlyselected from a substituted or unsubstituted C₃-C₁₀ cycloalkylene group,a substituted or unsubstituted C₁-C₁₀ heterocycloalkylene group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group; a1to a6 are each independently selected from 0, 1, 2, and 3; R₁ to R₆ areeach independently selected from a hydrogen, a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone, a carboxylic acid groupor a salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₂-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁)(Q₂), —B(Q₃)(Q₄), and—Si(Q₅)(Q₆)(Q₇); b1 to b6 are each independently selected from 1, 2, and3; c1 and c2 are each independently selected from 1, 2, and 3; whereinat least one substituent of the substituted C₃-C₁₀ cycloalkylene group,the substituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₂-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocyclolalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₁₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₁₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; a C₁-C₁₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —B(Q₁₃)(Q₁₄), and—Si(Q₁₅)(Q₁₆)(Q₁₇); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₁₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —B(Q₂₃)(Q₂₄), and—Si(Q₂₅)(Q₂₆)(Q₂₇); and —N(Q₃₁)(Q₃₂), —B(Q₃₃)(Q₃₄), and—Si(Q₃₅)(Q₃₆)(Q₃₇), wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ toQ₃₇ are each independently selected from a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent aromatic condensedheteropolycyclic group.
 2. The condensed cyclic compound of claim 1,wherein L₁ to L₆ in Formula 1A to 1C and 1E are each independentlyselected from a phenylene group, a pentalenylene group, an indenylenegroup, a naphthylene group, an azulenylene group, a heptalenylene group,an indacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isooxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzooxazolylene group, anisobenzooxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolyene group, animidazopyridinylene group, and an imidazopyrimidinylene group; and aphenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isooxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzooxazolylene group, anisobenzooxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolyene group, animidazopyridinylene group, and an imidazopyrimidinylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, an aC₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzooxazolylgroup, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group.
 3. The condensed cyclic compound of claim 1,wherein L₁ to L₆ in Formula 1A to 1C and 1E are each independently agroup represented by one of Formulae 3-1 to 3-32:

wherein, in Formulae 3-1 to 3-32, Y₁ is O, S, C(Z₃)(Z₄), N(Z₅), orSi(Z₆)(Z₇); Z₁ to Z₇ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino groups, a hydrazine, a hydrazone, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; d1 is an integer selected from 1 to 4; d2 is an integerselected from 1 to 3; d3 is an integer selected from 1 to 6; d4 is aninteger selected from 1 to 8; d5 is 1 or 2; d6 is an integer selectedfrom 1 to 5; and * and *′ are binding sites with adjacent atoms.
 4. Thecondensed cyclic compound of claim 1, wherein L₁ to L₆ in Formula 1A to1C and 1E are each independently a group represented by one of Formulae4-1 to 4-23:

wherein, in Formulae 4-1 and 4-23, * and *′ are binding sites withadjacent groups.
 5. The condensed cyclic compound of claim 1, wherein a1to a6 in Formula 1A to 1C and 1E are each independently 0 or
 1. 6. Thecondensed cyclic compound of claim 1, wherein R₁ to R₆ in Formula 1A to1C and 1E are each independently selected from a hydrogen, a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₂-C₂₀ alkyl group, a substituted or unsubstituted C₁-C₂₀alkoxy group, a substituted or unsubstituted C₆-C₂₀ aryl group, asubstituted or unsubstituted C₁-C₂₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, and —Si(Q₅)(Q₆)(Q₇).
 7. The condensed cycliccompound of claim 1, wherein R₁ to R₆ in Formula 1A to 1C and 1E areeach independently selected from a hydrogen, a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxylic acid group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₂-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup; a phenyl group, a pentalenyl group, an indenyl group, a naphthylgroup, an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group; aphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzooxazolylgroup, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a dibenzosilolyl group, a thiadiazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, each substituted with at leastone selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group,cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group; and Si(Q₅)(Q₆)(Q₇).
 8. The condensed cycliccompound of claim 1, wherein R₁ to R₆ in Formula 1A to 1C and 1E areeach independently selected from a hydrogen, a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxylic acid group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₂-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup; a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group,a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzooxazolyl group, a triazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group; and a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzooxazolyl group, a triazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group,a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzooxazolyl group, a triazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group.
 9. Thecondensed cyclic compound of claim 1, wherein R₁ to R₆ in Formula 1A to1C and 1E are each independently selected from a hydrogen, a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₂-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group and a group represented by one of Formulae6-1 to 6-49:

wherein, in Formulae 6-1 to 6-49, * is a binding site with an adjacentatom.
 10. The condensed cyclic compound of claim 1, wherein thecondensed cyclic compound is represented by one of Formulae 1A(1) to1A(3), Formulae 1A(5), Formulae 2A(1) to 2A(5), Formula 3A(1), andFormula 4A(1):

wherein, in Formulae 1A(1) to 1A(3), Formulae 1A(5), Formulae 2A(1) to2A(5), Formula 3A(1), and Formula 4A(1), R₁, R₂, b1, and b2 are the sameas those defined in claim 1, R_(3a) to R_(3g) are each independentlyselected from the same groups as those defined for R₃ in claim 1, R_(4a)to R_(4g) are each independently selected from the same groups as thosedefined for R₄ in claim 1, R_(5a) to R_(5g) are each independentlyselected from the same groups as those defined for R₅ in claim 1, andR_(6a) to R_(6g) are each independently selected from the same groups asthose defined for R₆ in claim
 1. 11. The condensed cyclic compound ofclaim 1, wherein the condensed cyclic compound is one of Compounds 1 to7:


12. An organic light-emitting device comprising: a first electrode; asecond electrode disposed opposite to the first electrode; and anorganic layer disposed between the first electrode and the secondelectrode and comprising an emission layer, wherein the organic layercomprises at least one of the condensed cyclic compounds of claim
 1. 13.The organic light-emitting device of claim 12, wherein the firstelectrode is an anode, the second electrode is a cathode, and theorganic layer comprises i) a hole transport region disposed between thefirst electrode and the emission layer and comprising at least one of ahole injection layer, a hole transport layer, a buffer layer, and anelectron blocking layer, and ii) an electron transport region disposedbetween the emission layer and the second electrode and comprising atleast one of a hole blocking layer, an electron transport layer, and anelectron injection layer.
 14. The organic light-emitting device of claim12, wherein the emission layer comprises the condensed cyclic compoundsof Formula 1A to 1C and 1E.
 15. The organic light-emitting device ofclaim 14, wherein the emission layer further comprises a phosphorescentdopant, and the condensed cyclic compounds serves as a host.